


Dressed Up

by heavydiirtysoul



Series: Underneath your clothes - crossdressing au [2]
Category: Twenty One Pilots
Genre: ( also tyler in dresses is my kink ok can u blame me ), Alternate Universe - High School, Alternate Universe - No Band, Blow Jobs, Crossdressing, ENJOY!!!, M/M, Public Blow Jobs, Smut, Tyler likes to wear dresses, and Josh likes to encourage Tyler to do exactly that, and it's all p cute until it also gets p hot ok, pastel!Tyler, that's all
Language: English
Status: Completed
Published: 2016-08-18
Updated: 2016-08-18
Packaged: 2018-08-09 13:41:38
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 3,154
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7804042
Author URL: https://archiveofourown.org/users/heavydiirtysoul/pseuds/heavydiirtysoul
Summary: <blockquote class="userstuff">
              <p>Tyler wants to buy a dress for his sisters birthday, and he's only trying it on to make sure it'll really fit her. Flirting with the cute shop assistant is an added bonus, fine, but the fact that he seems to really dig Tyler in this dress definitely won't have any influence on his decision wether to buy it. Not at all. Not the tiniest bit.</p>
            </blockquote>





	Dressed Up

Tyler wasn't a materialistic guy. 

He'd always liked vintage shopping; browsing through thrift shops and flea markets for hidden treasures was one of his favorite pastimes, so when he found the random flyer for a vintage shop summer sale at the school's blackboard, he didn't take long to decide that he'd go – he had nothing better to do anyways, and maybe he'd find a cute dress for his sister. It was her birthday in a few days, and he still hadn't figured out a good gift idea he liked, so he decided to go today, right after school. 

He waved goodbye to his friends, telling Mark to let his Dad at the bus stop at home know that he'd be late today, and off he was. The shop was close by, it only took him a few minutes of walking to get there.

 

The bell on the door of the shop was small and light, making the tiniest noise as he entered the store. It was the generic vintage shop, exactly the kind of place he'd spent hours in as a kid – Tyler had always had a faible for sundresses and pastel colors, getting giddily excited when he could help his mum or his sister pick out clothes. 

His parents had given him every chance to embrace his feminine side -- or any side, really, they were open and happy to let their son explore whatever he had set his mind on. His childhood was a happy time for him, limitless, free, his need to experiment and find himself in a world that was much too keen on restraining people in their personality always being supported by his family, so he was confident enough to walk into an all woman's shop without even bothering to care what others might be thinking. 

It was a well-sorted place, the dresses, skirts and shirts in order by color and size, and for a moment, Tyler could feel the familiar, childish excitement buzz in his fingertips – the fabrics were soft and silky as he let his hands dance over them, and he almost shuddered with nostalgia. 

He was drawn to the clothing rack with the violet, dark pink and magnolia dresses, eyes fixed on one specific piece with a laced up corsage, pretty valance cascading in waves, and it even had a petticoat in a soft, gleaming white, almost pearlescent. He eyed the dress curiously, itching to maybe try it on, but he couldn't find a salesperson to ask about it – he didn't want to come off odd, and sometimes, if the dresses were expensive, the shop wouldn't allow them to be tried, or only after buying them. 

Tyler didn't like those shops very much; while he could appreciate a store wanting to make the dress perfect with fitting it exactly to your own body after buying it, he couldn't really ask them to change the dress to fit the body of his sister without them knowing her measurements. He really hoped the shop he was in right now wasn't like that, since he really liked the dress and could see his sister wearing and loving it just as much.

 

„You're not the usual customer, I'll admit that.“ The voice caught Tyler off guard, and he almost dropped the dress, shoving it back onto the rack with a small jump. 

„Geez, you scared me“, he huffed, palm of his hand placed on his heart, turning around to find himself face to face with another guy, a bit older than himself, leaning against a rack with a smug grin. 

If there had ever been a guy that looked like he wouldn't be working in an all-woman's dress shop, this was him. He had bleached hair with a soft shimmer of blue, half washed out already, a nose ring, gauges and a full sleeve of tattoos, wearing skinny jeans, a NASA shirt, pink converse. Tyler knew he was staring, but he couldn't help it. 

"You don't look like the usual guy to work in a vintage dresses shop either." 

„Uh, okay, that's true, I guess.“ The other seemed to be utterly unimpressed with Tyler's obvious fascination, still leaning against the rack, casual. „So, can I help you with anything?“ 

„Sure“, Tyler muttered, reaching to grab the pastel-violet dress he'd picked out before, holding it up with raised eyebrows. He knew he was blushing, all the pride of confidence in his own femininity nothing more but a memory by now, standing in front of one of the most attractive guys he'd ever had the pleasure of laying eyes on. 

„I was wondering, um, so – actually, I need a gift for my sister. It's her birthday soon, and I think she'd really dig this one.“ He nodded towards the dress again, although it was obvious what he was talking about. „So, uh, she and I actually have pretty much identical measures, except for, you know – I don't really have... ah, whatever. Anyways, I was wondering, do you think I could try this on?“ 

He could feel the intense stare from the sales guy, and Tyler felt like squirming in place, like an ant under a looking glass, exposed. Maybe he'd just laugh and call him a pervert, just here to try on woman's clothes, kick him out, shake his head at the weirdo, but to his own suprise Tyler found the guy shrugging, then nodding casually. 

„Sure thing, can't think of a reason why you shouldn't. You might need help with the lacing though, so just call me when you want me to tie the thing up.“ 

The guy gestured towards the single small changing cubicle in the corner of the shop before taking the dress from Tyler and untangling the various bows and laces while Tyler stood next to him awkwardly, eyes everywhere but on the other guy's surprisingly delicate fingers working with the fabrics. 

„There you go“, he finally said, handing the dress back to Tyler and holding the curtain of the cubicle open for him, leaning against the frame again – always so casual, and Tyler almost envied the other guy for his radiating confidence. 

The heavy velvet curtain fell close, and Tyler could hear steps moving away. „I'm Josh, by the way. Just call when you need help.“ 

 

So now the guy had a name, and Tyler was glad to know it as he soon found himself all tangled up in countless fabrics – it was a mess, and he wasn't even sure if he had put the dress on the right way or if it was upside down or turned from the inside out. He was in his briefs only, one of the hooks of the corsage awkwardly stuck in the waistband of them, and he felt like crying - or maybe even hysterical laughter due to his own helplessness. 

„J – Josh?“ 

„Yeah?“, the voice came from the other end of the shop, and soon enough steps were closing in. 

„What's up? Need help?“ 

„Uh, I think so, yeah.“ 

„Okay, can I open the curtain? It's just you and me in the shop, don't worry.“ 

Tyler nodded before realizing Josh couldn't see him, so he took a deep breath to gather some confidence, popping his head out of the cabin first, slight blush and defensive expression on his face. 

„You have to promise not to laugh. I messed up pretty bad.“ 

„It's okay“, Josh nodded, serious undertone in his voice despite his huge grin, encouraging, almost. „Those dresses are complicated. No need to be ashamed. Now, come on, let me help you.“ 

Tyler pulled the curtain to the side, stepping out, half naked and covered in violet lace and silk, and the color surely didn't fit his excessive blush at all – but Josh looked somehow weirdly pleased, big eyes and honest admiration on his face. 

„The color suits you very well.“ 

Tyler wasn't sure if he was just being polite, but he suppressed a lame joke and remained silent, pressing his lips into a thin line while Josh worked the dress with trained hands and focused movements. 

„There you go“, he finally said, fingers ghosting over Tyler's waist for a moment as if he wasn't sure about what to do with his hands now that he was done. „I'm going to lace up the back real quick. Tell me if it's too tight.“ 

Soft fingertips were brushing against Tyler's back in a quick rythm, yet it didn't feel hurried, and every touch left the tiniest trace of a shudder on his skin, and he was sure that by this point Josh must've noticed the soft goosebumps on him. 

The other was silent, working, and when Tyler suddenly found himself being turned around by his waist to face the mirror, he couldn't help the gasp. 

 

The wavy fabric cascaded down his body in the prettiest ways, framing his thin shoulders with clouds of tulle, his waist almost perfectly curved into an hourglass shape, the huge bows on the circle skirt only amplifying the great effect the dress had on his figure. 

„You look stunning“, Josh said in a somehow muffled voice as if he was repressing something, and Tyler's eyes were as big as the moon as he gazed at himself in the mirror, unbelieving upon his own reflection. 

The fact that Josh was standing next to him, slightly to the back, drinking up his appearance in the mirror like he was dying of thirst only made the whole thing better, and Tyler almost giggled.  
„Are you okay?“, he asked, slightly poking fun at the other for his obvious admiration, batting his eyelashes in a very coquettish way, and Josh turned crimson red in a matter of seconds, turning on his heel immediately to walk away, and for a second Tyler thought he'd gone too far with their little game, feeling self-conscious and exposed suddenly. 

Anyone could walk in the shop at any moment, and he surely didn't want to be caught in a compromising situation like this, so he almost fled back into the cubicle, tearing the curtain close behind him with a quick, hasty motion. 

„Hey, wait, uh, – I don't even know your name.“ 

„Tyler“, he snapped, while already trying to fumble out of the dress, failing horribly thanks to the laced up back, „but why do you care?“ 

„Tyler, hi. Uh, I care because I have, um, I think it's the perfect addition for your dress – I mean, your sister's dress. Look.“ 

A shy hand sneaked through the curtain – stockings, delicate and softly glittering, with little bows on the top hem, and Tyler took them cautiously. 

„I – I'm not sure I'd need to try those on. I mean, stockings fit everyone, right?“ 

„Just do it, man. Gotta know they fit the dress, okay?“

 

Maybe it had just been an excuse, but Tyler agreed and slipped into the stockings – it felt weird at first, uncomfortable, but after a few moments of deep breaths and self-conscious gazes into the mirror of the cubicle he decided he'd just trust Josh with this. 

It did look cute, the way the stockings shaped his legs, making them look even tinier and more delicate than before, and Tyler couldn't help but notice how weirdly at home the whole outfit made him feel. He didn't feel like himself anymore, necessarily, more like someone else, someone prettier, someone coy and kittenish and flirtatious and definitely more feminine than he was usually in his basketball shorts and loose vests. 

He tiptoed out of the cubicle, making his way up to Josh silently, letting his hand ghost over Josh's shoulder for a moment, unsure if he should just pat him on it to get his attention, instead opting to lean in and whisper a soft 'Hey there, handsome' into the others ear. 

„Woah“, he made, a huffled noise as he almost jumped and hit his elbow on one of the clothing racks, and his eyes grew wide, scanning the thinly framed boy in front of him with surprise.  
„You look.. I mean, you're gorgeous. Your sister will love the dress, I'm sure.“ 

„Hm-mh“, Tyler made, twirling in front of the closest mirror, shooting short gazes across to Josh, beaming. „Or maybe I'll keep it for myself. I don't know.“ 

Josh nodded, seemingly absent-minded, lips pressed together in a thin line, and Tyler wondered for a brief second what was going on – but then Josh tried to low-key adjust his pants, and now it was Tyler's turn to worry his bottom lip between his teeth. 

„Umm, are you okay, Josh?“ 

„Sure thing. A-okay. All fine, don't worry“, he almost stumbled over his words, crimson red with embarassment as he noticed Tyler's gaze, and Tyler knew that Josh knew that he knew and all of that resulted in an awkward silence neither of them knew how to get rid of. 

„Uh, you could, um, help me out of the dress again, please“, Tyler muttered eventually, fingers nervously entangled in some of the lace bows on the skirt, and he avoided Josh's gaze, but the thought of being able to turn the other on with simple movements like twirling in a dress did give him a certain satisfaction. 

„Right. Yeah, sure. Let's go back to the cubicle, don't want to have you stand half-naked in the middle of the shop.“

 

The awkward silence continued as Josh's fingers ghosted over Tyler's back again, untangling the laced up back carefully with measured movements, and even though Tyler knew it wasn't helpful, he couldn't help the badly suppressed moan as Josh's fingers grazed his lower back. 

There were many things he'd expected as a reaction to that, but Josh throwing him around with a swift motion so his back crashed against the wall of the cubicle wasn't one of them. 

„Such a tease“, he muttered, Tyler's wrists caught in his hands, pushed against the wall above Tyler's head, and he was staring, mouth open wide upon the intense gleam of lust in Josh's eyes. „I -“, „Shh, princess. Now is not the time to talk, alright?“ Josh's voice was.. different, rougher, yet soothingly warm, like dark honey and coarsely ground coffee, and Tyler gasped sweet profanities as Josh's teeth left the tiniest marks on his neck. 

„Keep your hands where they are, princess“, Josh ordered, and it took Tyler his all to not let them fall down and into Josh's messy, blueish hair when he started to let his delicate hands wander up Tyler's thighs, softly tugging on the hem of the stockings. 

„So pretty, aren't you? Such a pretty princess. And so innocent, hm? Never been fucked in a dress before, have you?“ 

Josh's gaze locked with his, and Tyler shook his head slightly – he'd never been 'fucked' anywhere, and he articulated the thought, small voice, almost embarassed. Josh snapped out of the growly, seductive state immediately and gave Tyler big eyes, his hand cupping Tyler's cheek softly within the matter of a moment. 

„That's okay, shh. I have an idea.“ The gleam was back in Josh's eyes, and as he sunk down to his knees, thoroughly tugging on the stockings to bring them down and let Tyler step out of them, the younger boy had a very detailed idea of what exactly Josh wanted to do. 

He was almost painfully hard in his briefs now, and he couldn't help the squeal as Josh finally pulled down his underwear to let his dick spring free, pressing soft butterfly kisses to Tyler's inner thighs, and the tulle and silk shifting against their skin made them both weak in the knees. 

 

Where Josh's hands had been delicate and tender, his lips were rough and demanding without ever being too much – the stubble against his thighs was on the verge of being painful, burning harshly on sensitive skin, but the overwhelming mixture of pain and pleasure was enough to make the dressed up boy moan in the prettiest octaves. 

Josh's hand finally found the perfect pace around Tyler's cock, soft kisses ghosting on the head, short, quick flicks of a heavy, warm tongue against his slicked up skin.. Tyler was teary eyed with need at this point, whimpering breathless begs and sweet nothings. 

„Please, please, Josh, please“, an endless stream of muttered out words like a mantra was falling from swollen lips, worried between teeth, and his eyes were closed, the new, yet oddly familiar feeling of his nerves straining with sweet, close to unbearable ache numbing out every other sensation. 

Tyler wasn't even sure what he was begging for at this point, the movement of Josh's hands and his lips finally closing around Tyler's dick pushing him even closer to the edge, and he felt like collapsing into himself; into a panting, sobbing mess of blurred out vision and blood rushing in his ears. But Josh knew what he was doing, keeping Tyler on his toes, one hand reaching up to press him to the wall, keeping his hips in place and giving him no chance to buck up into Josh's mouth – even now, the older boy was completely in control, and Tyler was close to losing his mind with every nerve trembling to the point of breaking down completely. 

„Please, just let me--“, he muttered, and Josh hummed against the sweaty skin of his cock, tongue circling tiny patterns against hypersensitive skin, and before Tyler could object, Josh had gotten up again – the loss of contact for a mere second already caused him to whimper with pain, but Josh was leaning forward now, his whole bodyweight pressing against the younger boy.  
„I want to see you come,“, he whispered, soft smile tugging on his lips as he let his hand sneak under the layers of silk and lace, finally closing around Tyler's dick again, and Ty's head fell back against the wall with the overwhelming sensation of being so, so close, knots in his stomach, every inch of his body aching for release. 

„Look at me, princess. My pretty, dirty princess. Will you come for me? Would you do that for me, mh?“ 

And with a last few, quick strokes, Tyler could feel his every muscle tense, coming undone - falling apart beneath sloppy strokes from fragile, tender fingers and intense gazes from eyes as dark as the universe and just as pretty and maybe even just as dangerous if you got lost in them. 

Waves of pleasure were crashing into him and pulling him under, and for a second, he was sure he'd lose consciousness, unable to draw in just one breath. But Josh soothed him through his climax, hushed words and sweet nothings and soft, barely visible motions against his skin, tickling the last rushes of his orgasm out of him with practiced hands. 

Tyler collapsed against Josh's chest with a gasp, eyes wide, an exhausted smile plastered on his face as Josh trailed soft kisses along his collarbone. 

 

Needless to say, Tyler bought the dress; and his sister got a necklace for her birthday.

**Author's Note:**

> I just really like Tyler in dresses okay 
> 
> PROMPT ME @ www.badkittyjosh.tumblr.com
> 
> also shoutout to the wormler stans, y'all #duncumsquad


End file.
